Your Perfect Hilton Head Island Getaway Starts Here
Hilton Head Properties Realty & Rentals offers a diverse selection of Hilton Head vacation rentals to suit every type of traveler. From 1-bedroom villas for a quiet coastal escape to 7-bedroom vacation homes built for family reunions and group retreats, each property is thoughtfully furnished and ready for your stay. Guests can enjoy luxurious vacation amenities such as private pools, ocean views, and easy beach access in sought-after communities like Palmetto Dunes, Sea Pines, Forest Beach, and Folly Field.
These vacation homes and villas place you close to everything that makes Hilton Head Island special—championship golf courses, scenic bike paths, local dining, and Lowcountry charm around every corner. Each rental is backed by our experienced property management team, committed to delivering a seamless vacation experience from booking to check-out.
Spend your days relaxing by the pool, exploring the island, or enjoying the comforts of a professionally managed Hilton Head vacation home. With flexible options, top-rated amenities, and personalized service, Hilton Head Properties Realty & Rentals makes it easy to plan a stress-free Hilton Head Island vacation.
Start your search today and discover vacation rentals that bring comfort, style, and convenience together in one unforgettable island stay.
118 properties available
Elegant Oceanfront Penthouse Villa at Sea Cloisters3 Bedrooms | 3 Bathrooms | Sleeps 8 | Stunning Ocean ViewsATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2028 (Dates Subject to Change)Welcome to our elegant penthouse villa located in Hilton Head Island's renowned Sea Cloisters. This tastefully decorat
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Charming Turnberry Villa in Palmetto Dunes2 Bedrooms | 2 Bathrooms | Sleeps 6 | Two - StoryWelcome to our beautiful vacation home in Hilton Head Island! This spacious two-story villa offers comfort, style, and all the amenities you need for a perfect getaway.The villa features two suites with king beds, providing luxurious sleeping arrangement
Elegant Beachside Getaway Villa in Forest Beach2 Bedrooms | 2.5 Bathrooms | Sleeps 6 | Stunning ViewsWelcome to this beautiful Beachside Getaway, located in the perfect spot to enjoy all that Hilton Head Island has to offer! With all remodeled bathrooms, solid surface flooring, granite countertops throughout, smooth ceilings, and beautiful fur
Pet-Friendly Beach Villa in Stones Throw2 Bedrooms | 1 Bathroom | Sleeps 7 | Pet FriendlyWelcome to this beautiful beach-oriented villa in Hilton Head Island! Recently renovated to exceptional standards, this villa is sure to capture your heart. This 2-bedroom, 1-bath villa is the perfect vacation retreat, ready to provide you with an unforgettable
Stylishly Furnished Third Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsATTENTION: Building Construction during the time period of Sept 11, 2026 until March 19, 2026 (Dates Subject to Change)Welcome to Villa 309, a recently renovated and updated vacation home in Hilton Head Island that exceeds expecta
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Newly Remodeled Water Oak Villa in Palmetto Dunes3 Bedrooms | 3 Bathrooms | 1 Half Bathroom | Sleeps 10Welcome to 46 Water Oak Villa, a newly remodeled vacation home located in the heart of a charming sea-side village in Hilton Head Island. This two-story villa offers three oversized bedroom suites, making it an ideal choice for couples or families
Oceanfront First Floor Villa at Sea Cloisters3 Bedrooms | 2 Bathrooms | Sleeps 8 | OceanfrontATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2028 (Dates Subject to Change)Welcome to 113 Sea Cloisters—an oceanfront villa where comfort, convenience, and coastal beauty come together seamlessly.Perch
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
Top Floor Oceanfront Penthouse with Loft at Sea Cloisters3 Bedrooms | 3 Bathrooms | Sleeps 10 | Panoramic Ocean ViewsATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2028 (Dates Subject to Change)Welcome to Sea Cloisters 509, a magnificent oceanfront penthouse villa located on the top floor (5th floor) o
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
Third Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 5 | Ocean ViewsATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2028 (Dates Subject to Change)Welcome to your dream vacation home in Hilton Head Island! Located in the picturesque Folly Field area, this oceanfront villa offer
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Extensive Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2028 (Dates Subject to Change)Welcome to our newly renovated villa, where no expense has been spared to provide you with the very best beach experience.The villa b
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
Coastal Windsor Place II Villa with Breathtaking Ocean Views2 Bedrooms | 2 Bathrooms | Sleeps 8 | OceanfrontATTENTION: Elevator inoperable during the time period of Nov. 1, 2026 until March 20, 2027, due to the elevator being replaced (Dates Subject to Change) Welcome to this professionally decorated vacation home located on the fifth fl
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
Dog Friendly Huntington Villa in Palmetto Dunes3 Bedrooms | 3 Bathrooms | Sleeps 8 | Lagoon ViewsThis lovely Huntington villa has the "feel of a home". Nature lover? Enjoy the tranquil views of the 11 mile lagoon and the wildlife on the lagoon.Beach lover-you're only a 3-5 minute walk across the quiet street to the beach! Spacious ope
